This case study of school leaders in the Southern Philippines explored principal perspectives on local dynamics that facilitate and impede meaningful educational change. The research indicated that change is a complicated proposition in the region, and that some principals are better or worse equipped to lead depending on a variety of cultural, political and organizational factors. In particular, the research revealed that principals' ability to establish meaningful relationships with both school system and government officials was critical to facilitating positive change. The article concludes by making recommendations for local practitioners in the Philippines.